I've just completed Season 4. Barry is a tough one because Covid really damaged the momentum they had developed. In Season 1 we start with Barry, a soulless shell of a man who returns from the war empty and dead inside, but connected to his fellow soldiers by his now blossomed skill of being a ruthless killer. Returning to his father figure Fuches, a disturbed self-serving leach of a man, Barry begins a career as a hitman. This leads him to a fateful encounter with the acting class of Gene Cousineau, where Barry suddenly feels alive again and decides that acting will be the path that leads him to redemption. The next 3 seasons are simply following the story of Barry's tragic fate, as his past prevents his attempt to distance himself, and his character's flaws doom him.
During this journey, we have two separated worlds. There is Fuches and the mafia/gangland 'bad' guys, who provide us with complete absurdist humor and the core belly laugh moments of the show. On the other side, are the Hollywood wannabees of the trying-to-be-actors world, who provide us with irony, sarcasm, self-oblivious egoism, cowardice, bravado and lies. Barry, who maybe wants to be good, but simply isn't, navigates and attempts to balance the escalating absurdist plot devices that lead him deeper towards his tragic fate.
Ultimately, we learn that not a single character in this show was a good person. Barry, unable to change is doomed. Fuches, a needy prideful man chooses humanity. To me, Sarah Goldberg, who plays the love interest, Sally is the star of this show. She plays a hopeless vain, scared, desirous, self-serving, dishonest, needy egotistical woman and she is just awesome. How she didn't win an Emmy for this part escapes me. And at the end of the show, it seems that her character is the one that mattered. She is the one who emerges at the end a changed person...not better in anyway, but completely aware of her weaknesses and no longer naive about herself....she fully embraces her shallowness.
So what we get here is a pretty strong performance by Bill Hader, but the character itself is one note. Henry Winkler plays his role well, but the character is a despicable person. He is droll and oblivious, yet conniving at the same time. The humor surrounding the Gangsters is absurd. Some of it is plain funny, but overall it is simplistic and unrealistic. Ditto, with some of the police and Hollywood people. They allow the cheap gut laughs that the main characters wallowing in darkness can not give us.
At the end, the story comes to a too neat somewhat contrived conclusion. You kind of had hoped for something more lighthearted, but when there are no good guys, I guess it made sense.
It's not a truly great TV series, the timeline moves quickly over the four seasons, only Sally achieves any resolution, and the cheap nature of much of the humor spoils the higher aspirations that one had for the character arcs after Season 1. They got the horse across the finish line, but they didn't win the derby.